Hydrochloric Acid → (4-(Trifluoromethyl)benzyl)malononitrile

HRID 749598

Reaction equation

HRID 749598 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[C:8]([C:11]#[N:12])[C:9]#[N:10])=[CH:5][CH:4]=1.[BH4-].[Na+].Cl>C(O)C>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]([C:11]#[N:12])[C:9]#[N:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 714296(4-(Trifluoromethyl)benzylidene)malononitrileHCID 4311764Sodium borohydride

Product 1

HCID 10656743(4-(Trifluoromethyl)benzyl)malononitrileYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

First, 4.44 g of (4-(trifluoromethyl)benzylidene)malononitrile was dissolved in 20 ml of ethanol, and while stirring at room temperature, a suspension of 0.19 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloride acid was added to the reaction mixture, which became acidic and was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.30 g of (4-(trifluoromethyl)benzyl)malononitrile (the intermediate (4)).

Workup

  1. additionwas added dropwise
  2. stirringby stirring at room temperature for 30 minutes
  3. extractionwas extracted with diethyl ether
  4. washThe organic layer was successively washed with 10% hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8439fc2695e4fb0b52aae099c3403eb
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Linked notes

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